Furnished Apartments in Oldtown

Oldtown Serviced Apartments for Rent

When in Oldtown, relive the Victorian architecture and its effortless beauty in the most untouched form. With our furnished apartments in Oldtown, you are in for a full-fledged Chicago experience that keeps you near the local fun of the neighbourhood and the utmost comfort to welcome you back every night. With luxurious bedrooms and bathrooms, elaborate kitchens, modern aesthetics at its finest, and utmost comfort and privacy to complete everything, our furnished apartment portfolio is bliss for travelers of all tastes and nationalities. 

Some of Our Top Furnished Apartments in Oldtown are:

Each suite offers a high-end vibe to it. A bunch of apartments from our catalogue treat you with a gorgeous lake or unique city view right across from the balcony. With a service team, concierge desk, a kitchen full of appliances and groceries, and the most comfortable and timeless master bedroom to top it all, our exclusive Chicago portfolio is here to win hearts time and again. 

Where to Stay in Oldtown

Out of all the places, New Wells Street is your best pick when in Oldtown. From comedy clubs to nightclubs, tree-lined lanes full of outdoor restaurants to shopping, this street will not allow you a single dull moment. Old Town Triangle is a great spot to be in with the famous club Second City, historical remains, The Vig, Equinox, and much more. Any abode brushing with either of these iconic spots will ensure a memorable Oldtown experience.


Price Range




Microwave Oven
Washer / Dryer
Central Heating
Air Conditioning
Cots or Cribs
Work Desk
Private Garden
Secure Entry System
Carbon Monoxide Alarm
Gas Safety Check
Electrical Safety Check
Fire Certificates
Wheelchair Accessible
Onsite Restaurant
Pet Friendly
Smoking Allowed
Car Parking

Distance From City Center

Popular Neighborhoods

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Frequently asked questions

Things to know before booking serviced apartments in Chicago

There are over 8 serviced apartments in Oldtown Chicago with more being added every day. In total, TheSqua.re has over 250,000 apartments across the globe that are waiting to be booked. Book Now .

Prices start from £49 per night and increase from there. Bear in mind that the type of apartment and number of guest will affect the overall price. Book Now .

To see a selection of Oldtown Chicago offers, please visit our offers and coupon page .

Choose a part of Oldtown Chicago you want to visit and search for the perfect stay for you using our easy search tool. Begin your search here .

Some of the apartment buildings in Oldtown Chicago will offer bed and breakfast or gym membership, whereas others may provide them with an extra charge. The apartment listing will make that clear. Other services include airport pick-up, meet and greet and so much more. Book your stay here for the full TheSqua.re experience.

That depends on the policy of the apartment/building management. You may have to enquire first when making your booking in Oldtown Chicago.

Serviced apartments in Oldtown Chicago have all the features of home, are centrally located and have other astounding attributes that make them better than hotels, as covered here.

Oldtown Serviced Apartments for Rent

More About Oldtown,

Facts About Old Town

Squeezed between Lincoln Park and North Side is this highly acclaimed historic neighbourhood of Chicago, Illinois that dates back to 1872. With immigrant settlements, gay rights, and lots of Victorian-era buildings, Old Town is one impressive place to be in.

Some of the notable facts about Oldtown in Chicago include:

  • Old Town is home to one of the 7 historic buildings, St. Michael’s Church, which survived the Great Chicago Fire.
  • The 1960s and 1970s saw Old Town as the ultimate center of Chicago Folk Music.
  • It became the first “Gay Ghetto” of Chicago with innumerable gay bars and LGBTQ-friendly surroundings. 
  • Wells Street here came to be known as “The Porno Plague" (Time Magazine) in 1976 because of the increasing sex industries here. 

Weather in Old Town

With July as the hottest and the most month and January as the coldest and the snowiest, Old Town sees the best of both worlds. The Best Places Comfort Index annually stands at a glorious 7 for Oldtown. September, May, and June are the most welcoming and comforting months here with pleasant weather. The temperatures drop to a lower of 15 degrees in cold and rise to a whopping 86 degrees during intense summers which is one of the highest across Illinois. Overall, if you pick the right month after thorough research, Old Town will treat you with its best weather ever.